(3aS,4S,5S,8S,8aR)-8-methyl-3-methylidene-5-propan-2-yl-2,3a,4,6,7,8a-hexahydro-1H-azulene-4,5,8-triol

Details

• Internal ID: d1268bf1-6b9c-4be9-a85d-b4a22eff6bca
• Taxonomy: Lipids and lipid-like molecules > Prenol lipids > Sesquiterpenoids > Guaianes
• IUPAC Name: (3aS,4S,5S,8S,8aR)-8-methyl-3-methylidene-5-propan-2-yl-2,3a,4,6,7,8a-hexahydro-1H-azulene-4,5,8-triol
• SMILES (Canonical): CC(C)C1(CCC(C2CCC(=C)C2C1O)(C)O)O
• SMILES (Isomeric): CC(C)[C@]1(CC[C@]([C@@H]2CCC(=C)[C@H]2[C@@H]1O)(C)O)O
• InChI: InChI=1S/C15H26O3/c1-9(2)15(18)8-7-14(4,17)11-6-5-10(3)12(11)13(15)16/h9,11-13,16-18H,3,5-8H2,1-2,4H3/t11-,12-,13+,14+,15+/m1/s1
• InChI Key: QPSWXDQIUBPFIO-MRLBHPIUSA-N
• Popularity: 1 reference in papers

Physical and Chemical Properties

• Molecular Formula: C₁₅H₂₆O₃
• Molecular Weight: 254.36 g/mol
• Exact Mass: 254.18819469 g/mol
• Topological Polar Surface Area (TPSA): 60.70 Ų
• XlogP: 1.40
• Atomic LogP (AlogP): 1.86
• H-Bond Acceptor: 3
• H-Bond Donor: 3
• Rotatable Bonds: 1

Synonyms

There are no found synonyms.

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9881	98.81%
Caco-2	-	0.7408	74.08%
Blood Brain Barrier	+	0.6750	67.50%
Human oral bioavailability	-	0.5286	52.86%
Subcellular localzation	Mitochondria	0.5155	51.55%
OATP2B1 inhibitior	-	0.8511	85.11%
OATP1B1 inhibitior	+	0.9355	93.55%
OATP1B3 inhibitior	+	0.9128	91.28%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.9153	91.53%
P-glycoprotein inhibitior	-	0.9182	91.82%
P-glycoprotein substrate	-	0.8202	82.02%
CYP3A4 substrate	+	0.5332	53.32%
CYP2C9 substrate	-	0.7657	76.57%
CYP2D6 substrate	-	0.7344	73.44%
CYP3A4 inhibition	-	0.8262	82.62%
CYP2C9 inhibition	-	0.7201	72.01%
CYP2C19 inhibition	-	0.6835	68.35%
CYP2D6 inhibition	-	0.9373	93.73%
CYP1A2 inhibition	-	0.7242	72.42%
CYP2C8 inhibition	-	0.8965	89.65%
CYP inhibitory promiscuity	-	0.9157	91.57%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8700	87.00%
Carcinogenicity (trinary)	Non-required	0.6356	63.56%
Eye corrosion	-	0.9844	98.44%
Eye irritation	+	0.5433	54.33%
Skin irritation	+	0.5540	55.40%
Skin corrosion	-	0.9319	93.19%
Ames mutagenesis	-	0.7900	79.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6070	60.70%
Micronuclear	-	0.9400	94.00%
Hepatotoxicity	+	0.6078	60.78%
skin sensitisation	-	0.5859	58.59%
Respiratory toxicity	+	0.5889	58.89%
Reproductive toxicity	+	0.8000	80.00%
Mitochondrial toxicity	+	0.8625	86.25%
Nephrotoxicity	-	0.5543	55.43%
Acute Oral Toxicity (c)	III	0.5185	51.85%
Estrogen receptor binding	-	0.7227	72.27%
Androgen receptor binding	-	0.5280	52.80%
Thyroid receptor binding	-	0.6065	60.65%
Glucocorticoid receptor binding	-	0.6119	61.19%
Aromatase binding	-	0.5971	59.71%
PPAR gamma	-	0.8575	85.75%
Honey bee toxicity	-	0.8907	89.07%
Biodegradation	-	0.6500	65.00%
Crustacea aquatic toxicity	-	0.5900	59.00%
Fish aquatic toxicity	+	0.9817	98.17%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL253	P34972	Cannabinoid CB2 receptor	96.66%	97.25%
CHEMBL221	P23219	Cyclooxygenase-1	95.07%	90.17%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	94.17%	91.11%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	90.43%	96.09%
CHEMBL226	P30542	Adenosine A1 receptor	89.43%	95.93%
CHEMBL1994	P08235	Mineralocorticoid receptor	88.03%	100.00%
CHEMBL5608	Q16288	NT-3 growth factor receptor	86.12%	95.89%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.94%	94.45%
CHEMBL3137262	O60341	LSD1/CoREST complex	83.81%	97.09%
CHEMBL2996	Q05655	Protein kinase C delta	80.26%	97.79%
CHEMBL1871	P10275	Androgen Receptor	80.18%	96.43%

Plants that contains it

• Tephrosia vogelii

Cross-Links

• PubChem: 163070621
• LOTUS: LTS0021369
• wikiData: Q105225590